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Artículo

Experimental and theoretical insights into the formation of weak hydrogen bonds and H⋯H bonding interactions in the solid-state structure of two eucalyptol derivatives

Galvez, Carolina Elizabeth del ValleIcon ; Piro, Oscar EnriqueIcon ; Echeverría, Gustavo AlbertoIcon ; Robles, Norma LisIcon ; Lezama, José Osvaldo GuyIcon ; Sankaran, Sankaran Venkatachalam; Thamotharan, Subbiah; Villecco, Margarita Beatriz; Loandos, Maria del HuertoIcon ; Gil, Diego MauricioIcon
Fecha de publicación: 03/2022
Editorial: Royal Society of Chemistry
Revista: New Journal of Chemistry
ISSN: 1144-0546
e-ISSN: 1369-9261
Idioma: Inglés
Tipo de recurso: Artículo publicado
Clasificación temática:
Química Orgánica

Resumen

Two eucalyptol derivatives, namely 1,3,3-trimethyl-2-oxabicycle[2.2.2]oct-5-yl acetate (4) and 1,3,3-trimethyl-2-oxabicycle[2.2.2]oct-5,8-yl acetate (6) have been synthesized and characterized. Their crystal structures have been solved by single-crystal X-ray diffraction methods indicating that the molecular conformation of both compounds is stabilized by intramolecular C-H⋯O bonds between the H-atoms of the methyl group from the eucalyptol moiety and the O-atom of the acetoxy group. In addition, we have performed a detailed investigation of the intermolecular interactions that stabilize the crystal packing of both structures by using Hirshfeld surface analysis and their associated two-dimensional fingerprint plots. The analysis reveals that the solid-state structure of compounds 4 and 6 is mainly stabilized by C-H⋯O hydrogen bonds and H⋯H bonding interactions. These interactions have also been described and studied energetically using DFT calculations. The nature and strength of these intermolecular contacts have been rationalized by using several computational tools including molecular electrostatic potential (MEP) surfaces, natural bond orbital analysis (NBO), Bader's theory of atoms in molecules (QTAIM) and non-covalent interaction plot (NCI plot) index methods. Furthermore, the intermolecular contacts observed in the crystal lattice of both compounds were experimentally studied through vibrational (IR and Raman) and 1H and 13C NMR spectra. The computational molecular docking analysis of the compounds has been carried out against five potential leishmanial drug targets and the main protease of SARS-CoV-2.
Palabras clave: INTERMOLECULAR INTERACTIONS , CRYSTAL STRUCTURE DETERMINATION , NMR SPECTROSCOPY , QUANTUM CHEMICAL CALCULATIONS
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info:eu-repo/semantics/restrictedAccess Excepto donde se diga explícitamente, este item se publica bajo la siguiente descripción: Creative Commons Attribution-NonCommercial-ShareAlike 2.5 Unported (CC BY-NC-SA 2.5)
Identificadores
URI: http://hdl.handle.net/11336/207078
DOI: http://dx.doi.org/10.1039/D2NJ00428C
URL: https://pubs.rsc.org/en/content/articlelanding/2022/NJ/D2NJ00428C
Colecciones
Articulos(IFLP)
Articulos de INST.DE FISICA LA PLATA
Articulos(INBIOFAL)
Articulos de INSTITUTO DE BIOTECNOLOGÍA FARMACEUTICA Y ALIMENTARIA
Articulos(INQUINOA)
Articulos de INST.DE QUIMICA DEL NOROESTE
Citación
Galvez, Carolina Elizabeth del Valle; Piro, Oscar Enrique; Echeverría, Gustavo Alberto; Robles, Norma Lis; Lezama, José Osvaldo Guy; et al.; Experimental and theoretical insights into the formation of weak hydrogen bonds and H⋯H bonding interactions in the solid-state structure of two eucalyptol derivatives; Royal Society of Chemistry; New Journal of Chemistry; 46; 12; 3-2022; 5690-5704
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